Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1995-11-02
1997-09-09
Kight, John
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 185, 536 187, 53612313, 562433, 530395, C07H 504, C07H 1512, C07C22900
Patent
active
056658761
DESCRIPTION:
BRIEF SUMMARY
The invention concerns 3-(aminoacyl-amino)-saccharides and processes for their preparation from 3-amino-allo-saccharose.
Linkings of amino acids and saccharides are mainly present in glycopeptides and glycoproteins and, to a small extent, also in bacterial lipopolysaccharides. In the case of glycopeptides, it is a question of partial structures which occur as linkage region of saccharides and proteins in glycoproteins. Glycoproteins, which are to be found in soluble form in the blood and in numerous secrets, as well as in fixed form in membrane double layers, have, in recent times, achieved interest since their function has been recognised and investigated in biological control processes. In many cases, the carbohydrate side chains serve as recognition signal.
The nature of the covalent bonding between protein and carbohydrate side chain scarcely differs, however, in spite of the great number of naturally-occurring glycoproteins, which is caused by the biosynthesis of the glycoproteins. The two components are linked via a glycosidic bond, whereby one differentiates between N-glycoproteins and O-glycoproteins. In the case of the N-glycoproteins, the side chain amide group of an asparagine component is mostly linked .beta.-N-glycosidically with 2-acetamido-2-desoxy-D-glucose. However, in addition, in recent times, there have also been found N-glycosyl sud N-galsctosyl structures. In the case of O-glycoproteins, there is mostly present an .alpha.-O-glycosidic linking of 2-acetamido-2-desoxy-D-galactose or a .beta.-O-glycosidic linkage of D-xylose with a hydroxyl group of serine or threonine (H. Paulsen, Synthesen, Konformationen und Rotgen-struktureanalysen von Saccharidketteh der Core-Regionen von Glycoproteinen, Angew. Chem. 102 (1990) 851-867; H. Kurtz, Synthese von Glycopeptiden - Partialstrukturen biologischer Erkennungskomponenten, Angew. Chem. 99 (1987) 297-311; J. Montreuil, Primary Structure of Glycoprotein Glycans, Adv. Carbohydr. Chem. Biochem. 37 (1980) 157-223).
Individual amino acids have also been detected in lipopolysaccharides of bacterial origin which are linked via an amide formation with aminosugars, e.g. N-acetyl-glycine, which is bound via the amino group of 4-amino-4,6-didesoxy-D-glycopyranosyl radical to the O-specific side chain of the lipopolysaccharide of Shigella dysenteriae type 7 (Y. A. Knirel et al., Carbohydr. Res. 179 (1988), 51-60), or N-acetyl-L-serine which is bound via the amino group of the 3-amino-3,6-didesoxy-D-glucopyranosyl radical with the O-specific side chain of the lipopolysaccharide of Escherichia coli 0114 (V. L. L'vov et al., Carbohydr. Res. 112 (1983) 233-239). These substances act antigenically.
The invention refers to new 3-(aminoacyl-amino)-saccharides of the following formula I, ##STR2## in which R.sup.1 signifies hydrogen, a carboxyl group or a phenyl group or an alkyl group with 1-10 C-atoms which is possibly substituted by a phenyl, carboxyl, hydrozyl, mercapto or amino group, whereby the said substituents are possibly provided with protective groups, R.sup.2 is hydrogen, an amino protective group usual in peptide chemistry or a peptide group and R.sup.3 represents hydrogen or a fructosyl group, n=0 or 1, especially 3- (L-aminoacyl-amino)-D-allopyranosyl-.beta.-D-fructofuranoside in the following designated as 3-(aminoacyl-amino)-allo-saccharose, and 3-(L-aminoacyl-amino)-D-allopyranose. Furthermore, the invention includes preparation processes for these materials starting from 3-amino-3-desoxy-D-allo-pyranosyl-.beta.-D-fructofuranoside, briefly called 3-amino-allo-saccharose.
In the case of the 3-(aminoacyl-amino)-allo-saccharides according to the invention, it is a question of materials in which the carboxyl group of an amino acid is bound via an acid amide binding to the amino group of the 3-amino-allo-saccharose. Thus, in contra-distinction to the glycoproteins, these compounds contain no glycosidic bond between carbohydrate and amino acid but rather show a similar bonding structure to the above-mentioned lipopolysaccharides.
The 3-(aminoacyl-amino)
REFERENCES:
patent: 4472379 (1984-09-01), Suami et al.
patent: 5463022 (1995-10-01), Inoue et al.
Kochetkov et al., Izv. Akad. Nauk SSR, Ser. Khim., vol. (2): 367-371, (1967).
Kunz, Synthese von Glycopeptiden, etc., 1987, 297-311.
Paulsen, Synthesen, Konformationen, etc., 1990, 851-867.
Kiyozumi, Eine Verbesserte, etc., 1970, 355-365.
Pietsch, Untersuchungen zu Stabilitat, etc., 1993, 70-73.
L'vov, 3-[(n-Acetyl-1-Seryl)Amino]-3,6-dideoxy, etc., 1982, 233-239.
Montreuil, Primary Structure of Glycoprotein Glycans, etc., Advances in Carbohydrate Chemistry and Biochemistry, vol. 37, 157-223.
Knirel, Somatic Antigens of Shigella, etc., 1988, 51-61.
Buchholz Klaus
Noll-Borchers Martina
Pietsch Martina
Kight John
Lee Howard C.
Verein der Zuckerindustrie
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